


How Not To Matchmake

by slartibartfast



Category: Supernatural
Genre: Community: help_haiti, Fluff, Het, Humor, M/M, Matchmaking, Slash
Language: English
Status: Completed
Published: 2010-03-06
Updated: 2010-03-06
Packaged: 2017-10-07 18:33:09
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,498
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/67984
Author URL: https://archiveofourown.org/users/slartibartfast/pseuds/slartibartfast
Summary: <blockquote class="userstuff">
              <p>Sam and Anna conspire to bring Dean and Castiel together. ...It doesn't go so well.</p>
            </blockquote>





	How Not To Matchmake

**Author's Note:**

  * For [tangodoodles](https://archiveofourown.org/gifts?recipient=tangodoodles).



**Step One: Initiation**

 

"Sam," Anna said, "we have to talk."

It was about the most ominous start to a conversation possible, especially when one half of the discussion was going to be conducted by a powerful angel who was currently wiggling her fingers to beckon him closer. Sam raised his eyebrows and glanced at Dean, but his brother was busy across the room explaining to Castiel some pop culture reference he'd made earlier, leaving Castiel gazing at him in a thoroughly bemused way.

So with Dean too distracted to save him from this portentous parley, Sam followed Anna into the kitchen with his hands in his pockets and his steps slow. "What is it?" he asked.

He and Anna had never talked much since she decided to stick around and help them, so the conspiratorial smile she gave him was a surprise. "Dean and Castiel."

"What about them?" Sam asked.

She arched an eyebrow. "Don't tell me you haven't noticed, Sam. You'd have to be an idiot not to."

Sam wondered if he should be offended, but then with a sinking feeling in his stomach he realized what this was about. Dean and Castiel, as in _Dean and Castiel_. Together. With the moony eyes and the veiled discussions and the possessive closeness. He'd hoped not mentioning it would make it go away. "Oh. Oh, I guess... oh. Why do we need to talk about it? It's nothing to do with me."

"They're gonna do this dance for the rest of time if we don't help them along," Anna said. Sam was kind of relieved to know that Dean and Castiel weren't already at it in secret; that would be even more awkward than this frankly cringe-worthy situation. "So what do you say?"

A dramatic pause. "I have no idea what you're talking about," Sam admitted.

Anna folded her arms. "I know my brother. I know he doesn't have a clue that he's flirting with Dean, but I know he wants it and has done since he met the guy."

"This is really awkward," Sam said hesitantly.

"And you," Anna continued as if he hadn't spoken, "know Dean better than anyone. He's into Cas, yeah?"

"Oh, definitely." Sam hadn't ever seen anyone get to Dean so quickly. It had been a long time since Sam had given up the ghost that maybe it was the whole angel deal that was putting that look in Dean's eyes.

"Then we need to help them."

Sam sighed. "This isn't gonna end well."

 

**Step Two: Conspiracy**

 

"I think we should fly ahead of you," Anna said at the start of a hunt. Sam was already in the car and Dean was slinging the bags in the back. Castiel looked up with his face impassive.

"Why?" asked Dean. Sam scoffed; his brother spent most of the time they were in the car complaining about lugging around two angels anyway.

Anna smiled and shrugged as if the thought had just occurred to her. Sam looked away and tried not to grin at how ridiculous this all was. "I don't know, I thought maybe Cas and I could check out the scene, get some research done so we're ready to hunt by the time you get there this evening."

Dean slammed the boot shut and glanced at Castiel, who was beginning to look vaguely suspicious, though you'd need a microscope to see it. Dean shrugged in a stilted attempt at nonchalance and got into the car. "Great. See you there," he said, and rumbled the engine into life.

"We have no need to go ahead of them," Castiel said once they were gone, dust kicked up from the dry ground and setting a muddy tint to the air.

Anna patted his shoulder. "I know, Cas. I wanted to talk to you. Alone."

Castiel didn't look any less suspicious. "We are not going to have sexual intercourse, Anael."

"Wait, what?" Anna said, thoroughly derailed. "I don't want to have sex with you. What the hell?"

"I assumed," Castiel said, turning briefly to look at the disappearing car. He had the good grace to lose the suspicious squint at least. "You have been watching me for the past three days more than is socially acceptable in these bodies. I grew uncomfortable, and-"

"Let me guess," Anna interrupted. "You asked Dean for advice."

Castiel stared like she'd plucked the thought from his mind. He paused for a flustered second and changed the subject. It took so little to ruffle his feathers these days. "Then what did you want to talk about?"

Anna resisted the urge to prod and tease and instead straightened out the amused lines of her face. "Dean."

"What has he done?"

"Nothing."

"Then why must we talk about him?"

Apparently this was going to be difficult, since Castiel had yet to work out what Anna wiggling her eyebrows meant. "You like him."

"He is an admirable person," Castiel replied slowly. "He has many good qualities."

"And quite a few bad ones," Anna added, and smiled appeasingly when Castiel bristled. "Hey, it's okay. Dean's a good person, you're right. That's what I wanted to talk about."

That constipated grimace of suspicion returned threefold. "Then it is Dean with whom you wish to fornicate."

Anna rolled her eyes. "I'd say 'got the t-shirt' but I'm pretty sure you're still not up to scratch on cultural idioms."

"I have no idea what you're talking about," said Castiel, becoming impatient. "But I do know that if you and Dean wish to reinitiate your physical relationship, it has nothing to do with me."

He spread his wings and Anna didn't bother stopping him.

"That went well," she told the empty parking lot, and followed a moment later.

\---

Anna caught up with Sam in the bathroom of a gas station zipping up his jeans. He stumbled back, only just managing not to lose his balance which was a seriously good thing as he didn't particularly feel like grabbing at the mold-spotted walls. "Jesus Christ," he spluttered. He was pissed off enough not to bother apologizing for the blasphemy.

"C'mon, Sam, I walked through the door," she pointed out, smirking.

"Yeah but I was expecting a guy," Sam said, glancing down to check his fly was properly secured. "I thought you can't tell where we are?"

"I followed Cas," she explained. "He's out there with Dean who told me where you are."

Sam seemed to relax a little. Apparently this intrusion of privacy was totally okay if it was to do with setting up his brother with an angel, and no, he wasn't going to over-analyze that particular train of thought. "How did it go?"

Anna scrunched up her nose and Sam was almost one hundred percent sure it wasn't to do with the off-putting stench of the unclean toilets. "Not great. He thought I was telling him I'm screwing Dean."

"Yeah, at least you got that far," Sam said gloomily as he ran his hands under the ice-cold water. "I managed to get in one comment about how Castiel's around a lot lately and he turned up the music so loud I'm going to be partially deaf for the next three weeks."

"Great. Our brothers are idiots," she replied. "We're gonna have to do something about this, Sam. The unresolved sexual tension is getting distracting."

"I don't know. Maybe we should just drop it. Dean's gonna notice eventually."

"Really?" Anna raised her eyebrows.

Sam sighed. "Okay, no, he's master of denial. Fine. You'd better have a less stupid plan this time."

"I'd like to see you do better," snapped Anna.

"Not exactly difficult," Sam said. "Seriously, were you really head of an angel garrison? Your strategic skills are severely lacking."

Anna smacked him in the arm. It hurt. "I _will_ smite you."

Sam laughed and ignored the flutter low in his stomach when she touched his arm to blink them both out of there and back to the car.

 

**Step Three: Coercion**

 

In the morning, Anna lied. It was a sin but she'd become quite good at those lately, Sam had noticed. She was taking to moral relativity better than a duck to water, though she had better wings if her bragging was anything to go by.

"I've gotta check on Beniel," she said. "He's been brought down from the North and re-stationed in Chicago. He was one of the less idiotic members of my garrison and might be able to tell me something about the angel's plans."

"Beniel would never betray heaven," Castiel said. "He remains loyal."

"We were close once," Anna said. It was the truth, and Sam felt a pang of regret for her; he would probably turn her in if she were truly intending to approach him, but Castiel didn't know that. "I'll be safe, and I'll be back soon."

"Yeah, I uh," Sam started once she disappeared, then paused. Both Dean and Castiel had turned to him wide-eyed. The intensity of it was a little disconcerting, especially since Sam hadn't had a chance to drink any of the coffee in front of him. It was way too early to be properly devious. "I'm gonna head back to the room, guys. I think I ate something bad."

He scuffled out of there quickly, wishing he'd grabbed some of the food before he skipped out. Oh well; at least the plan was in place.

\---

"Did you have a nice breakfast?" Sam asked when Dean returned forty minutes later.

Dean dropped his bag down on the floor and shut the door. "Dude, you are acting really fucking weird lately, you know that right?"

"I don't know what you're talking about." Sam did his best not to be too obvious. He wasn't very good at it and ended up catching himself squirming awkwardly. "I'm uh, feeling better. Now."

"That's great," Dean said. He passed Sam a box. It was still warm. "I saved your food. Cas heated it up again."

Sam held the box in his hands, the soft scent of pancakes rising from it. He swallowed hard and looked back up. "Thanks. Is Castiel okay?"

"Sure, why wouldn't he be?"

"I dunno. You two don't get much time together, that's all," Sam said, putting the leftover food to the side for the moment even though his stomach was rumbling like a bitch.

"Yeah, not until the last couple of days," Dean said. At Sam's alarmed look, he smirked. "C'mon Sammy, you think I'm stupid? Where is Anna anyway?"

"What? In Chicago," Sam replied, clueless. He was suddenly very certain he'd missed a step in this conversation.

Dean punched his arm on the way past the chair in the exact spot Anna had hit before. It was still sore and Sam grimaced. Dean laughed. "I know, dude. I don't care, okay? It's kinda cute. She's way out of your league, though. Clearly the fact me and her are over has made her lower her expectations."

"You had sex, you weren't life partners," Sam snapped, and then mentally slapped himself. That was so not the point here. "Wait. Fuck, Dean, I'm not sleeping with Anna."

"Seriously? What do you two do when you _sneakily_ leave together? You know what, I bet you sit and have deep conversations about the ethics of fluffy puppies of something." In fact Anna and Sam _had_ recently had a conversation about puppy mills and Dean quickly picked up on Sam's pause to mean confirmation of his suspicions. With a triumphant grin on his face, Dean walked into the bathroom. "I knew it. You've really gotta work on subtlety, dude."

Sam opened his mouth to protest but the bathroom door was already shut. At the click of the lock, Sam sagged back in his chair and huffed a frustrated breath. "This is so not going how I imagined it," he muttered, and went to meet Anna outside.

 

**Step Four: Admit Defeat**

 

"I don't think this is going to work," Anna said apropos of nothing.

Sam looked up from the laptop. Anna was blurred around the edges and it took him rather too long to work out that it was because he'd been staring at the screen for the best part of four hours researching a demonic creature that no one seemed to have a clue about, not even the goddamn angels. He was tired. Exhausted. Really fucking ready for bed, actually, and now Anna wanted a conversation. "Huh?" he said, and hoped the general gist got through the formless syllable.

Anna sighed. It was more of a sad sigh than a frustrated sigh, but then sometimes Sam couldn't tell. "I said I don't think this is going to work," she repeated as if that would somehow make Sam magically understand. She rolled her eyes after receiving a blank look and sat beside him on the bed, legs tucked under herself. "Dean and Castiel. I don't know, maybe we were wrong."

They certainly seemed impervious to their most devious plans and their most rubbish ones, too. Sam had even got Dean drunk and asked whether he'd ever thought about kissing a dude and Dean had quickly dragged his drunk ass home to bed, loaded up with tap water. That had been two nights ago. Sam wasn't sure he'd slept more than three hours since.

"Maybe," said Sam, which was about as much conversation as he could manage. Anna pressed down the laptop screen. Sam only just managed to get his fingers out of the way in time. "Hey!"

"Pay attention," Anna snapped. "We need to know if this is working."

"It isn't," Sam said, and then leaned back from the vitriolic glare he received in response. "What? It isn't working, Anna, you know that. They remain as clueless as ever."

The silence stretched out for a little while. Anna was pretty close, Sam noticed in that sleep-hazy way. She smelt cold and fresh, like she'd been standing in a frozen wasteland for a few hours. Come to think of it, Sam hadn't seen her for a day or so. Her appearance now was the first he'd seen of her in a while and he'd assumed she was with Dean and Castiel, hunting out this creature while Sam complained about insomnia and spent most of the time researching fruitlessly.

"Where have you been?" he asked. "Are you okay?"

"Yeah," said Anna, then fidgeted. Their arms were pressed together now and Sam was pretty sure he wasn't supposed to notice that, so he tried not to. "I wanted Cas to have some happiness, you know? I encouraged him down this path and being an angel without Heaven behind you is pretty awful. I should have thought about it more. I thought if I could get him with Dean, maybe... I don't know."

Sam frowned. "It isn't your fault things turned out this way."

Anna laughed. "Right. But I didn't help. It doesn't matter, Sam. It's too late to do anything about it now."

"I don't think he's unhappy," Sam said, though of course it was difficult to tell with his blank stares. Not like Anna, who Sam could read so easily and right now, he could see that her disappointment was born of a deeper sorrow. His heart ached for her and maybe he couldn't make his brother hook up with his angel boyfriend, but he could comfort her. "Don't smite me, okay?" he muttered and let his arm drop around her shoulders.

For a moment Anna was tense and her wide eyes turned on him with accusation and confusion. It didn't last. She searched his tired stare and seemed content with whatever she found, a smile settling into place, warm as the sunset red in the sky outside the window.

They leaned together, Anna's head on Sam's shoulder, and the smile on Anna's face didn't fade.

 

**Step Five: The Big Reveal**

 

"Holy shit."

Sam woke with a jolt and realized with something akin to horror that he had been asleep. That in itself was a good thing, but the fact he'd been practically cuddled up to Anna at the time was a little less of a good thing.

He sat up straight and Anna moved with him. Her eyes were open and she looked as alert and focused as usual; if Sam wasn't mistaken, she hadn't slept. The thought summoned up a strange warmth in him. He had no idea how long he'd been wrapped up in sleep but however long it had been, Anna hadn't moved.

"Okay, seriously dude," Dean said, and Sam snapped his head around in surprise. In his sleep-filled confusion, he hadn't realized the startled words had come from his brother. Dean was disheveled and splattered with blood and beside him, just as pristine as ever, Castiel stood. Dean's mouth was open. "I _knew_ that was why you two have been spending so much goddamn time together."

"What?" Sam asked. His mouth tasted like year old socks, dry as the desert.

Anna untucked herself from the cradle of Sam's arm and rose elegantly to her feet. "We're not sleeping together, Dean," Anna said.

Oh.

"We suspected you were attempting to get us to - " Castiel hesitated and glanced sideways at Dean, " - 'hook up'. It wasn't clear that it was in fact you two indulging in a physical relationship."

"Fuck, you guys have got it so wrong, that's not –"

"Wait, you _knew_?" The interruption startled Sam and he got the feeling Anna had picked up on something he hadn't. No surprise there. Her mouth was halfway between a grin and a gape and yet she still managed to look composed. It really wasn't fair.

"Then you were?" Dean asked. "I knew it!"

It was beginning to get a little too opaque for Sam's sleepy mind and he frowned, struggling to follow the conversation from his half-slouched position on the bed. And then Castiel cleared it all up as tactfully as ever. "Dean and I consummated our relationship three months and four days ago."

_Oh_.

Sam stared. "You mean this was all for nothing." When Dean just grinned, Sam turned to Anna for solace. "Please tell me I'm dreaming. This is some cracked out nightmare, right? You were together before we even started."

"Yeah, and gotta say, your efforts were _weak_," Dean said.

With a groan, Sam flopped back against the pillow and closed his eyes. All that effort for nothing and since when had Dean become sneaky? Dean was the kind of guy to announce loudly and obnoxiously that he had successfully achieved mutual orgasm with just about anyone, let alone an angel. Surely that was the kind of thing Dean would have boasted about, unless it was more than just sex.

That sobering thought didn't get much of a foothold, though, when Sam met Castiel's eye a moment later and Castiel narrowed his. "How long have you been having intercourse with Anna?"

Sam's life sucked. It was official.

 

**Step Six: The Sort-Of Happy Ending**

Okay, so it didn't suck completely.

Sam grinned at the look on Bobby's face as the mismatched group trailed up to the house. There was Castiel and his placid stare, hair even more of a mess than usual ("I like the bed-hair," Dean had insisted after repeatedly ruffling it in the car) and Dean at his side, smug smirk and his arm draped around Castiel's waist. And then there was Sam himself and his own angel, her shining red hair smelling of the cheap shampoo they'd shared in the shower that morning. Her hand was cool where their fingers were laced together.

Turned out they were rubbish matchmakers, but it wasn't a complete waste of time. They were closer than ever, a team custom built to stop the apocalypse and, preferably, have lots of awesome sex in the meantime. In separate rooms, since it would be inconvenient for Sam to insist they have separate states, however tempting after the first time they had neighboring rooms. Apparently Cas was a screamer.

Bobby gaped and let them past two by two. They had a lot of work to do but that didn't stop Bobby from grilling them thoroughly on whether they'd been near any curse boxes lately, maybe pissed off a witch. It took a lot to convince him that no, Winchesters were just _really_ good at seducing angels, if not matchmaking.

"Fine. You've all lost your damn minds but fine," Bobby said eventually.

All four of them grinned as Bobby shook his head and left the room muttering about what idiots they all were to fetch some books. Well, three of them did. Castiel hadn't quite got that down yet; his smile was small but earnest.

"Okay. No making out at the table," Sam said. "And no more matchmaking."

"Good, 'cause you two failed so hard at that."

Sam smacked his brother's arm across the table. "The game was rigged!"

It didn't matter now, though. Maybe Dean was right; they were awful matchmakers but that didn't matter. It was worth it in the end.


End file.
